For somebody so embedded into the news cycle, I agree that Tim has resisted a Blue>Red flip pretty well. It just seems to be the inevitable as the Left moves further that direction. What story is that last straw? I agree that the possibility of losing a good part of his base listeners is a scary thought, but he should be thinking about how popular that story would be to people with more conservative ideals. I would think it would be a net gain in listeners wanting to not just bubble in with FOX/Shapiro stanced people, and get a bit of news from a more Central-Right recent convert.
It seems to me though that it is not only happening to people in the news, or on YT. People with followings, etc. As example, I had a friend that would sit and sing/busk in popular nightlife areas, mostly anti-war songs, during the prime Iraq/Bush years. People would spit on him, call him all kinds of crazy names, really some similar actions to the current Left, but never any dangerous violence. Even with that type of reception, he would just keep on doing his thing, strumming away. Classic Left ideals and action, non-violent to the core. Even this guy now has said he won't ever vote Trump, but would greatly consider a Red vote with how extreme and past the 60's-90's Left ideals their party has gone. IMO the Left's only hope is to bring in people from other places and legislate their right to vote, or indoctrinate young minds.